28092-62-8

Usage

Uses

Used in Pharmaceutical Industry:
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione is used as an antifungal agent for its inhibitory effects on the growth of certain fungi. Its unique molecular structure makes it a promising candidate for further drug development research in the pharmaceutical industry.

InChI:InChI=1/C19H18N2O3/c22-18-17-16(13-24-18)20(11-14-7-3-1-4-8-14)19(23)21(17)12-15-9-5-2-6-10-15/h1-10,16-17H,11-13H2/t16-,17-/m0/s1

Upstream product

• 28092-55-9 6ξ-acetoxy-1,3-dibenzyl-(3ar,6ac)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 102225-85-4 [S]-1,1-di-(3-thienyl)-2-propanol 
• 40222-70-6 1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride 
• 22875-81-6 3,3-diphenyl-butan-2-ol 
• 1055329-67-3 (4S,5R)-1,3-dibenzyl-5-(propargyloxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 
• 1055329-68-4 (4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic acid 
• 100-46-9 benzylamine 
• 83889-77-4 (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid 
• 634188-84-4 (3aS,6R,6aR)-1,3,5-tribenzyl-6-hydroxytetrahydro-4H-pyrrolo[3,4-d]imidazole-2,4(1H)-dione 
• 100-39-0 benzyl bromide 
• 159912-63-7 (3aS,6aR)-tetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 83889-76-3 (4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 
• 26339-42-4 (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 
• 95790-99-1 cis 1,3-Dibenzyl-4-hydroxy-2,3,3a,4,6,6a-hexahydro-furo<3,4-d>imidazol-2-one 

Downstream Products

• 133709-72-5 cis 1,3-Dibenzyl-4-(hex-5'-enyl)-4-hydroxy-2,3,3a,4,6,6a-hexahydrofuro<3,4-d>imidazol-2-one 
• 133709-73-6 trans 1,3-Dibenzyl-4-(hept-6'-enoyl)-5-hydroxymethylimidazolidine-2-one 
• 56198-32-4 cis-1,3-dibenzyl-4,5-dihydroxymethyl-imidazolidin-2-one 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 156910-19-9 (3aS,6aR)-1-Benzyl-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 133709-77-0 cis 1,3-Dibenzyl-4-(1'-methylthiothiocarbonyloxyhept-6'-enyl)-5-benzyloxymethylimidazolidin-2-one 
• 133895-53-1 Methanesulfonic acid (S)-1-((4S,5R)-1,3-dibenzyl-5-methanesulfonyloxymethyl-2-oxo-imidazolidin-4-yl)-pentyl ester 
• 133709-90-7 cis 1,3-Dibenzyl-4-(1'-methylthiothiocarbonyloxypentyl)-5-benzyloxymethylimidazolidin-2-one 
• 133709-70-3 cis 1,3-Dibenzyl-4-(1'-methylthiothiocarbonyloxypentyl)-5-t-butyldimethylsilyloxymethylimidazolidin-2-one 
• 133709-83-8 cis 1,3-Dibenzyl-4-(5'-carboxypentyl)-5-benzyloxymethylimidazolidin-2-one 
• 133709-76-9 cis 1,3-Dibenzyl-4-(1'-hydroxyhept-6'-enyl)-5-benzyloxymethylimidazolidin-2-one 
• 133709-82-7 cis 1,3-Dibenzyl-4-(5'-formylpentyl)-5-benzyloxymethylimidazolidin-2-one 
• 133709-89-4 cis 1,3-Dibenzyl-4-(1'-hydroxypentyl)-5-benzyloxymethyl-imidazolidin-2-one 
• 133709-78-1 cis 1,3-Dibenzyl-4-(hept-6'-enyl)-5-benzyloxymethylimidazolidin-2-one 

Relevant academic research and scientific papers

METHOD FOR PRODUCING AMIDE CARBOXYLIC ACID COMPOUND, AND METHOD FOR PRODUCING AMIDE ALCOHOL COMPOUND, AND METHOD FOR PRODUCING LACTONE COMPOUND

PROBLEM TO BE SOLVED: To provide a production method for efficiently obtaining a high-purity amide carboxylic acid compound, which is useful as a synthetic intermediate of biotin. SOLUTION: In a method for producing an amide carboxylic acid compound, an anhydride of a specific ureido compound is brought into contact with an optically active amine such as N-Me-R-α-methyl benzyl amine to obtain a mixture comprising an amide carboxylic acid compound, and then, the amide carboxylic acid compound is isolated from the obtained mixture. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Practical Synthesis of (+)-Biotin Key Intermediate by Calcium Borohydride Reduction and Temperature-Dependent Purity Upgrade during Crystallization

An expedient synthesis of a key intermediate for (+)-biotin has been accomplished through high-yielding reduction of chiral imide with calcium borohydride and efficient isolation of the desired isomer by crystallization at a specific temperature where only undesired isomer was converted to soluble anhydrate while the desired isomer kept unchanged as a less soluble monohydrate.

Method for stereoselectively synthesizing chiral lactone, chiral compound and application of chiral compound

The invention relates to the field of organic synthesis, and discloses a method for stereoselectively synthesizing chiral lactone, a chiral compound and application of the chiral compound in synthesis of biotin. The method comprises the following steps: (1) carrying out first reaction on cyclic anhydride, cyclic chiral alcohol and organic alkali tertiary amine to obtain dicarboxylic acid mono-ester quaternary ammonium salt; (2) carrying out second reaction on the dicarboxylic acid mono-ester quaternary ammonium salt and a reducing agent after intermediate treatment or no intermediate treatment to obtain alcohol acid; and (3) under an acidic condition, carrying out a third reaction on the alcohol acid to obtain the chiral lactone shown in the formula (I). According to the method disclosed by the invention, the target product can be obtained with high selectivity and high yield.

HYDRATE OF AMIDOALCOHOL COMPOUND, PRODUCTION METHOD THEREOF, AND PRODUCTION METHOD OF LACTONE COMPOUND

PROBLEM TO BE SOLVED: To provide a hydrate of an amidoalcohol compound, which is an intermediate raw material of biotin synthesis, a production method thereof, and a production method of a lactone using an amidoalcohol compound. SOLUTION: A hydrate of an amidoalcohol compound is represented by a formula (I). (In the formula, R1 and R2 are each a substituted/unsubstituted benzyl group, R3 is a substituted/unsubstituted phenyl group, and n is 0-1.) SELECTED DRAWING: None COPYRIGHT: (C)2022,JPOandINPIT

METHOD FOR PRODUCING LACTONE COMPOUND

PROBLEM TO BE SOLVED: To provide a production method that produces a lactone compound, an important intermediate in biotin production, with high purity and efficiency. SOLUTION: A method for producing a lactone compound includes bringing an amide alcohol compound represented by the formula (1) (where R1 and R2 may be different from each other to represent a substituted or unsubstituted benzyl group, R3 is a substituted or unsubstituted phenyl group) into contact with hydrogen chloride in a solvent including an aprotic polar solvent. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Synthetic method of (3S,6R)-1,3-dibenzyltetrahydrofuroimidazole-2,4-dione

The invention discloses a synthetic method of (3aS,6aR)-1,3-dibenzyltetrahydrofuroimidazole-2,4-dione. The method uses a cyclic anhydride as a starting raw material, and the cyclic anhydride is subjected to selective alcoholysis, reduction and cyclization to prepare the chiral lactone (3aS,6aR)-1,3-dibenzyltetrahydrofuroimidazole-2,4-dione. The process route is simple, raw materials are cheap andreadily available, the diastereoselectivity of an alcoholysis reaction is high, a chiral alcohol reagent can be recovered and applied through simple extraction, and the production cost is reduced. Themethod has the advantages of simple and convenient operation, mild reaction conditions, high yield, and good stereoselectivity, and has relatively good application values and economic benefits.

Method for stereoselective synthesis of chiral lactone

The invention relates to the field of organic synthesis, and discloses a method for stereoselective synthesis of chiral lactone. The method includes the following steps: (1) carrying out a first reaction on cyclic anhydride represented by formula (1), chiral alcohol represented by formula (2) and an organic alkali tertiary amine represented by NRRR in the presence of a protective gas anda solvent to obtain a quaternary ammonium salt represented by formula (3); (2) carrying out a second reaction on the quaternary ammonium salt represented by the formula (3) and a reducing agent to obtain a quaternary ammonium salt of alcohol acid, represented by formula (4); (3) carrying out a third reaction on the quaternary ammonium salt of the alkyd, represented by the formula (4), and an alkaline substance to obtain a metal salt of the alkyd; and (4) carrying out a fourth reaction on the metal salt of the alkyd to close the ring. The method for stereoselective synthesis of chiral lactone can achieve recovery of chiral alcohol and the organic tertiary amine at a high recovery rate without using expensive lithium hydroxide, and can obtain the target product at a high yield.

Novel asymmetric synthesis method for biotin chiral lactone

The invention discloses a novel asymmetric synthesis method for biotin chiral lactone. According to the method, by taking cycloanhydride as an initial raw material, the chiral lactone (3S,6R)-1,3-dibenzyl tetrahydrofuroimidazole-2,4-dione is prepared by selective alcoholysis, reduction and cyclization. The method is simple in process route, the raw material is cheap and easily available, and an alkaline catalyst is nearly insoluble in water and is recycled and reused through simple extraction, so that the production cost is lowered, and the diastereoselectivity of the alcoholysis reaction is improved. The method has the advantages of being simple to operate, mild in reaction condition, high in yield and high in stereoselectivity and has relatively good application value and economical benefits.

Process development and scale-up for the preparation of roche thiolactone: Key intermediate for (+)-biotin

The main objective of this paper was to report a short and efficient synthesis of Roche thiolactone starting from cis-1,3-dibenzyltetrahydro-2H-furo-[3,4-d]-imidazole-2,4,6-trione (2) with an overall yield of 74%. The optimized synthetic route consists of three chemical steps and the final process of thiolactonization of (3aS,6aR)-lactone 4 using xanthate ionic liquid in solvent-free conditions to furnish Roche thiolactone 1 not only features the yield improvement of 1 by optimizing reaction variables but also highlights simplifying the subsequent workup procedure.

Method for Producing Intermediate of Biotin and Method for Producing Biotin

In the method, a trione compound represented by the following formula (1) is (i) reduced by NaAlH2(OCH2CH2OCH3)2 and subsequently further reduced by a metal borohydride salt, or (ii) reduced by calcium borohydride, thereby producing an amide alcohol compound represented by the following formula (3) (wherein, R1 and R2 may be the same or different and each represents a hydrogen atom or a protecting group of an ureylene group; R4 represents an alkyl group, an aralkyl group, or an aryl group; and each of R5, R6, and R7 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom).